Sodium Iodide → 7-(2,5-Dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one

HRID 1700643Notes

Reaction equation

HRID 1700643 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:26])=[CH:5][C:6]=1[CH:7]1[CH2:12][C:11]([NH:13][NH:14]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:10][C:9](=[O:25])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:34][C:35](=O)[CH3:36].[I-].[Na+]>COCCOC.CO>[Cl:1][C:2]1[S:3][C:4]([Cl:26])=[CH:5][C:6]=1[CH:7]1[CH2:12][C:11]2[N:13]=[N:14][CH:34]=[C:35]([CH3:36])[C:10]=2[C:9](=[O:25])[CH2:8]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 183175305-(2,5-Dichlorothiophen-3-yl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one

Product 1

HCID 183174407-(2,5-Dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-oneYield 52.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(2,5-dichlorothiophen-3-yl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (1.33 g), anhydrous potassium carbonate (1.14 g), chloroacetone (0.4 g), sodium iodide (0.3 g), methanol (25 ml) and 1,2-dimethoxyethane (10 ml) was stirred at 80° C. for 3 hours. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified with silica gel column chromatography to give 7-(2,5-dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one (0.51 g) as colorless crystals.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-a8b200322ef0446380401c22f4c8069a
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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